Dating back to the 1840s, H. Upmann is among the oldest cigar brands still in use today. It began in the early 1840s when Herman Upmann left his position as a banker to establish a branch office in Havana. Upmann soon understood that he might start a business in the field, and in 1844 he made the audacious decision to invest in a cigar factory, formally launching the H. Upmann brand.

 Both the Upmann bank and the cigar company went bankrupt later in 1922, and they were forced to sell to J. Frankau & Co., a British company that carried on producing the cigars until 1935, when the brand was once more sold to the newly founded Menendez y Garcia Co., who produced the well-known Montecristo cigar. Up until the tobacco sector was nationalised following the Cuban Revolution, the new owners carried on producing H. Upmann cigars.

All of H. Upmann's sizes are "tripa larga, totalmente a mano"—long filler, completely handmade—and their mix is made up only of filler and binder tobaccos cultivated in the Vuelta Abajo zone.

The brand's branded boxes have gold medals from at least eleven international shows throughout the 19th century